Wine and derivatives run a lot of software very well, but indeed run a minority of it very poorly or not at all. Microsoft and Adobe software are the primary candidates for not running even slightly, and if they do, they definitely do not work right. If you need that software, there is no particular sign that Wine will run it well any time soon, though it will run some of it sort of okay. I've tried quite a bit of it. If you need that software, then you will need Windows, at least in a VM.
Specialized software either works great or fails pathetically with little in between IME. Drivers can be a big problem though, because the software can be looking for the drivers very specifically. If you have Windows software to go with hardware whose interface dongle is not mostly just a ch340 or something, you are probably gonna have a bad time.
Practically everything works great with Linux these days, though. Standards have mostly won and Linux is taken seriously. OSS is now also generally taken seriously and even preferred in solutions large and small. The dependency on closed standards and platforms is waning, and while that's no comfort to anyone forced to run Windows for some compatibility reason now, at least it's becoming less of a problem. Even people who think Windows is fine now recognize that they don't want to be stuck with a dependency on a specific version of it.